methyl hepta-O-benzyl-β-cellobioside

Base Information

• Chemical Name: methyl hepta-O-benzyl-β-cellobioside
• CAS No.: 82805-17-2
• Molecular Formula: C₆₂H₆₆O₁₁
• Molecular Weight: 987.199
• Mol file: 82805-17-2.mol

Synonyms:methyl hepta-O-benzyl-β-cellobioside

Chemical Property of methyl hepta-O-benzyl-β-cellobioside

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of methyl hepta-O-benzyl-β-cellobioside

There total 51 articles about methyl hepta-O-benzyl-β-cellobioside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + (2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran (92470-93-4) → methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (64694-18-4,77117-44-3,81307-79-1,82805-15-0,82805-16-1,82805-17-2,82805-18-3,84799-76-8,114817-97-9,114817-98-0,117894-99-2,123806-51-9,123877-32-7,117894-98-1)

Guidance literature:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; (2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran; With silver(l) oxide; In dichloromethane; at 0 ℃; for 0.166667h; Molecular sieve; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.201905576

Reference yield: 92.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + 1-O-(((1-ethynylcyclohexyl)oxy)carbonyl)-2,3,4,6-tetra-O-benzyl D-mannopyranoside → methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (64694-18-4,77117-44-3,81307-79-1,82805-15-0,82805-16-1,82805-17-2,82805-18-3,84799-76-8,114817-97-9,114817-98-0,117894-99-2,123806-51-9,123877-32-7,117894-98-1)

Guidance literature:

With tris(2,4-di-tert-butylphenyl)phosphiteAuCl; silver trifluoromethanesulfonate; In dichloromethane; at 25 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

DOI:10.1002/anie.201511695

Reference yield: 92.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + 1H-benzo[d][1,2,3]triazol-1-yl 2,3,4,6-tetra-O-benzyl α-D-mannopyranoside → methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (64694-18-4,77117-44-3,81307-79-1,82805-15-0,82805-16-1,82805-17-2,82805-18-3,84799-76-8,114817-97-9,114817-98-0,117894-99-2,123806-51-9,123877-32-7,117894-98-1)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.joc.7b02027

upstream raw materials:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride

Thiophosphoric acid O,O'-dimethyl ester O''-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl) ester

methyl 4-{1-[2-(((2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy)methyl)phen-1-yl]vinyl}-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Refernces

• 1、 Geringer, Scott A.,Singh, Yashapal,Hoard, Daniel J.,Demchenko, Alexei V.. "A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide–Triflic Acid Catalysis". . p. 8053 - 8063. Retrieved 2020/06/05.
• 2、 Kowalska, Karolina,Pedersen, Christian Marcus. "α-Selective glycosylations using glycosyl: N-(ortho-methoxyphenyl)trifluoroacetimidates". supporting information. p. 1918 - 1925. Retrieved 2020/03/23.